Epirubicin
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| Epirubicin
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| Systematic (IUPAC) name | |
| 10-(4-amino-5-hydroxy-6-methyl-oxan-2-yl) oxy-6,8,11-trihydroxy-8-(2-hydroxyacetyl)- 1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione | |
| Identifiers | |
| CAS number | |
| ATC code | L01 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C27H29NO11 |
| Mol. mass | 543.519 g/mol |
| Pharmacokinetic data | |
| Bioavailability | NA |
| Protein binding | 77% |
| Metabolism | Hepatic glucuronidation and oxidation |
| Half life | ? |
| Excretion | Biliary and renal |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status | |
| Routes | Intravenous |
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Ongoing Trials on Epirubicin at Clinical Trials.gov Clinical Trials on Epirubicin at Google
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US National Guidelines Clearinghouse on Epirubicin
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Overview
Epirubicin is an anthracycline drug used for chemotherapy. It is marketed by Pfizer under the trade name Ellence in the US and Pharmorubicin elsewhere.
Similarly to other anthracyclines, epirubicin acts by intercalating DNA strands. Intercalation results in complex formation which inhibits DNA and RNA synthesis. It also triggers DNA cleavage by topoisomerase II, resulting in mechanisms that lead to cell death. Binding to cell membranes and plasma proteins may be involved in the compound's cytotoxic effects. Epirubicin also generates free radicals that cause cell and DNA damage.
Epirubicin is favoured over doxorubicin, the most popular anthracycline, in some chemotherapy regimens as it appears to cause fewer side-effects. Epirubicin has a different spatial orientation of the hydroxyl group at the 4' carbon of the sugar, which may account for its faster elimination and reduced toxicity. Epirubicin is primarily used against breast and ovarian cancer, gastric cancer, lung cancer, and lymphomas.
Development history
The first trial of epirubicin in humans was published in 1980.[1] Upjohn applied for FDA approval in node-positive breast cancer in 1984, but was turned down because of lack of data.[2] It appears to have been licensed for use in Europe from around this time however.[3] In 1999 Pharmacia (who had by then merged with Upjohn) received FDA approval for the use of epirubicin as a component of adjuvant therapy in node-positive patients.
Patent protection for epirubicin expired in August 2007.
References
External links
- http://www.bccancer.bc.ca/HPI/DrugDatabase/DrugIndexPro/Epirubicin.htm
- http://www.pfizeroncology.com/products/ellence.aspx
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
